Acetonitrile → N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine

HRID 474262Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474262
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.[CH:19]([N:22]([CH:25](C)C)CC)(C)[CH3:20].C(#[N:30])C>>[Cl:1][C:2]1[N:3]=[C:4]([NH:30][CH2:20][CH2:19][NH:22][CH3:25])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

Komponenten

4

Edukt 3

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 580754242,4-Dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[D]pyrimidine

Produkt 1

HCID 86668110N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamineAusbeute 70,6 %

Versuchsvorschrift

To a solution of 2,4-dichloro-7-(4-fluorophenyl)-6,7-dihydro-5H cyclopenta[d]pyrimidine (2.0 g, 7.06 mmol) in acetonitrile (50 mL) was added diisopropylethylamine (1.369 g, 10.60 mmol) followed by N-1-methylethane-1,2-diamine (0.628 g, 8.48 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and the residue was taken in dichloromethane (10 mL) and silica (2 g). The resultant slurry of the compound on silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, 10% methanol in chloroform) to get N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine (1.6 g, 70.6%) as a light brown solid. LC-MS (M+H)+=321.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.13 (2H, br s), 7.22-7.11 (4H, m), 4.21-4.17 (1H, t, J=8.0 Hz), 3.82-3.79 (2H, m), 3.27 (3H, s), 3.19-3.04 (4H, m), 2.55-2.54 (1H, m), 1.99-1.98 (1H, m).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-087692eff4cd4c39a4346fb4f6758ced
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637523B2

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